Behind The Business Insights – 2016 Conference Presenter, Sheila E. Lewis

Photo - Sheila LewisFor our first Behind the Business Insights, we are talking to one of this year’s conference presenters, Sheila Lewis.  Since starting her first company, Flyin’ West LLC, in 1997, Sheila has fully embraced the journey of being an entrepreneur, experiencing the ups with the downs and the challenges along with success.  Taking the time to grow through the process of “figuring it out,” she started her second company Ashton212 LLC in 2012 with her business partner, Mary Ann Munro. This a boutique consulting firm providing specialized talent through four practices to global Fortune 1000s, mid-cap and small businesses, educational institutions, and large non-profit organizations.  This multi-million dollar business entity is headquartered in Oakland, Calif.

Sheila will be presenting the workshop,” Getting Real About Starting and Running a Business,” and here is a little preview to some of the insights and information that she will share.

1.  When starting on your journey as an entrepreneur, what were your initial thoughts and perceptions about being in business for yourself?

I don’t know that I actually thought about it in a deliberate sense. What I thought about was that I was tired of corporate and that I had been an early job jumper.  Much like people do today, I was doing 30 years ago when it was pretty much unheard of. So I had five years of great experience in three different industries.  I wasn’t the traditional vice president that had 15 cumulative years in one industry.  I knew from a skills and performance perspective that I should have been considered for positions at that level, since I’d held them before, but I kept getting pushed into director level positions.  And so without having the 15 years of linear experience in one industry, which by the way would have bored me to tears, I decided to try to sell my brain and started a strategic marketing consultancy.

I really went into business in 1997 thinking I would do it for three to five years and then I would return to corporate.  When I took the opportunity, I found that I didn’t look like them anymore.  To them I was even more of an oddity because I had been out for what was at that time 10 + years and I was considered an entrepreneur. I found that unless it was a company that really appreciated the entrepreneurial spirit in all of its goodness, they (corporate) looked at me and other entrepreneurs and thought, “Um, that may be problem waiting to happen.”

Having always been a person who interviewed and got the job, this reality was somewhat difficult for me. I was interviewing for jobs that I knew I could do and not getting them.  So I actually hired a coach who was more of a life coach and he asked me a lot of hard questions.  I reached a point through this coaching relationship where I had an epiphany which was as much as they (corporate) might want to consider me for a job, I had to want them. It was likely showing up in the interviews that I might not really want them after all and that I was simply trying to fit into their company and do the job as it was written in a job description.  Energized by this revelation, I decided that if I was going to be an entrepreneur, how was I going to build my business and how big did I want my business to be. Those were my immediate challenges and it wasn’t until 15 years into the business that I finally figured out how to do it which lead to the development of Ashton212.

2.  Looking back now as a seasoned entrepreneur, what would you tell yourself as a younger entrepreneur about starting, running and growing a business?

Have a plan.  Definitely have a plan.  Consider the longer term of being on your own.  Also, understand there are limits to how much you can earn as a consultant on your own.  I made a lovely living and I ended up expanding my model to include other people who I was making money on while they were working but it took a toll on me after a few years. I, like many solopreneurs providing a professional service, was hunting, killing, feeding, writing proposals, working engagements, and paying the bills … really everything. And so, I would tell my younger self to be very clear about what your financial goals are and what’s your exit strategy and when might you start to pivot and go back into the corporate life.

3. Tell us about one or two challenges that you have had to face and overcome as a small business owner?

It is all people driven.  If you are going from being a solopreneur to having employees, that is a shift.  I am not a control freak, I am quality freak and I am an expectations person. I have very high expectations of myself and of anyone who works with me.  They don’t have to do it my way but they have to do it well.  I am looking for them to use their own juice and their own DNA which should complement or challenge mine so that we actually end up being better.  It is finding those people that is the biggest challenge. Those who really do understand the entrepreneurial spirit and instincts and understand you have to kind of feel like you are an owner of the company; you need to roll up your sleeves to do whatever needs to be done; you need to work really smart and be prepared for the success of what you do in a very tangible and immediate kind of way.

4. Please share one or two successes that you have enjoyed as a small business owner.

Just the very fact that I did it.  For years I said, “I can’t figure it out.  I can’t figure out how to scale my company” and I spoke negative words into the universe and they embraced me. So I stayed hostage in the thought that I could not do it which is the antithesis of who I am.  My older brother said, “You are a new product development person. You are a business and marketing strategist. You do this for Wells Fargo, you do this for Levi Strauss. You’ve done this for Quaker Oats, you’ve done this for The Limited, figure it out.” And so I turned my business into a project for me and I gave it as much TLC as I gave projects for paying clients. Doing that gave me the time and energy to figure out how to grow my business.  So the success for me is jumping from “I can’t do it” to “Oh, heck yeah you can and you did!”

Another success that I would point to is getting to the multi-million dollar level and my goal is way bigger than where we are now. Only 3% of women-owned businesses in this country generate more than $1M in annual revenue. I’m delighted to be among them.

The last success is showing up for other entrepreneurs and making the time to share whatever I can that might help them move to the next level with their business.  I love entrepreneurs.  I think we’re a little crazy and incredibly passionate.  We love the challenge of getting it done, but we also need encouragement and we need to see role models who have done it.

5.  What is the number one lesson or tip that you would share with small business owners that can help grow their businesses as well as put them on the path to long term success? 

I could answer this question in ten different ways, but I will try to answer it in a couple.  One is to ensure you are surrounded by people who bring a perspective that is different than your own. They can be an advisor, a coach, a mentor, an advisory board of two or three people who have a different lens on your business.  The results are found in the collaborations that then take place.  Your willingness to allow someone else to speak into your business, who you trust and who can help you will pay dividends.

The second thing that I will say is just don’t give up, be courageous. Dare to be successful.

To hear more of Sheila’s insights about starting and running a business, be sure to register for this year’s Behind the Business Conference hosted by Cuisine Noir in San Francisco on September 17.  For more information and to register, visit

For more information about Sheila Lewis and Ashton212, visit

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About VSheree

V. Sheree Williams is the publisher of Cuisine Noir Magazine, the country's first digital and print culinary magazine that connects the African diaspora through food, drink and travel. For more, in-depth stories, visit
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